Heterocyclic amide derivatives

ABSTRACT

The present invention relates to novel heterocyclic amide derivatives of the formula  
                 
 
     in which R 1 , R 2 , R 3  and R 4  are as defined in the disclosure,  
     to a process for preparing them, and to their use as pesticides.

[0001] The present invention relates to novel heterocyclic amidederivatives, to processes for preparing them and to their use aspesticides.

[0002] It is known that certain 1-benzylamino-, 1-benzylideneamino- and1-benzoylaminoimidazoles have pharmacological properties (cf. EP-A-283857). Use of the substances specified therein as pesticides is, however,not described.

[0003] The invention now provides novel compounds of the formula (I)

[0004] in which

[0005] R¹ and R² independently of one another represent hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, represent optionally substitutedcycloalkyl, represent optionally substituted heterocyclyl or, togetherwith the carbon atoms to which they are attached, represent anoptionally substituted mono- or bicyclic, carbocyclic or heterocyclicgroup.

[0006] R³ and R⁴ independently of one another represent aryl or hetaryl,each optionally substituted.

[0007] It has additionally been found that the novel compounds of theformula (1) are obtained if compounds of the formula (II)

[0008] in which

[0009] R¹, R² and R³ are as defined above

[0010] are reacted with compounds of the formula (III)

R⁵—COR⁴  (III)

[0011] in which

[0012] R⁴ is as defined above and

[0013] R⁵ represents halogen (especially chlorine) or hydroxyl

[0014] in the presence of a diluent and an acid acceptor and/or acarboxylic-acid-activating reagent (coupling reagent) and optionally abasic reaction auxiliary.

[0015] Finally it has been found that the novel compounds of the formula(1) possess strongly pronounced biological properties and are suitablein particular for controlling animal pests, especially insects, spidermites and nematodes which occur in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienesector.

[0016] A general definition of the compounds of the invention is givenby the formula (1).

[0017] Preferred substituents and ranges of the radicals set out in theformulae mentioned above and below are elucidated in the following text:

[0018] R¹ and R² independently of one another preferably representhydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₃-alkyl,C₁-C₃-alkylthio-C₁-C₃-alkyl, represent in each case optionallyC₁-C₃-alkyl-substituted C₃-C₇-cycloalkyl, which may optionally beinterrupted by one or two oxygen and/or sulphur atoms, or, together withthe carbon atoms to which they are attached, represent optionallyC₁-C₃-alkyl-substituted C₃-C₄-alkanediyl, in which two carbon atoms thatare not directly adjacent optionally form a further cyclic structurewhich may optionally be interrupted by one oxygen and/or sulphur atom.

[0019] R³ preferably represents phenyl or hetaryl in each caseoptionally substituted once or twice by identical or differentC₁-C₄-alkyl, C₁-C₄-alkoxy, halogen, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,cyano, nitro, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, thioamide ortetrazole substituents (for example pyridyl, thienyl, furyl,pyrimidinyl).

[0020] R⁴ preferably represents phenyl in each case optionallysubstituted from one to four times by identical or differentC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, halogen,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano substituents, in each casetwo adjacent carbon atoms optionally forming a five- or six-memberedcarbocycle which may optionally be interrupted by one or two oxygenatoms, or hetaryl (for example pyridyl, thienyl, furyl, pyrimidinyl).

[0021] R¹ and R² independently of one another with particular preferencerepresent hydrogen, C₁-C₅-alkyl, C₁-C₃-alkoxy-C₁-C₃-alkyl,C₁-C₃-alkylthio-C₁-C₃-alkyl, represent C₃-C₆-cycloalkyl or, togetherwith the carbon atoms to which they are attached, representC₃-C₄-alkanediyl in each case optionally substituted from one to threetimes by identical or different C₁-C₃-alkyl substituents and in whichtwo carbon atoms not directly adjacent optionally form a further cyclicstructure which may optionally be interrupted by an oxygen or sulphuratom.

[0022] R³ with particular preference represents phenyl, pyridyl,thienyl, furyl or pyrimidinyl in each case optionally substituted onceor twice by identical or different methyl, fluorine, chlorine, bromine,iodine, cyano, nitro, methoxy, trifiluoromethyl, trifluoromethoxy,sulfonylmethyl, sulfonyltrifluoromethyl, thioamide or tetrazolesubstituents.

[0023] R⁴ with particular preference represents phenyl in each caseoptionally substituted from one to four times by identical or differentmethyl, ethyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy,trifluoromethoxy, ethoxymethyl ether or cyano substituents, two adjacentcarbon atoms optionally forming a five- or six-membered carbocycle whichmay optionally be interrupted by one or two oxygen atoms.

[0024] R¹ with very particular preference represents hydrogen or methyl,

[0025] R² with very particular preference represents hydrogen, methyl,ethyl, n- or isopropyl, n-, iso- or s-butyl, cyclopentyl, or cyclohexyl,or

[0026] R¹ and R², together with the carbon atoms to which they areattached, with very particular preference represent C₃-C₄-alkanediyloptionally substituted once or twice by methyl or representC₄-alkanediyl in which two carbon atoms not directly adjacent optionallyform a further cyclic structure which may optionally be interrupted byan oxygen atom,

[0027] R³ with very particular preference represents phenyl optionallysubstituted once or twice by identical or different methyl, fluorine,chlorine, bromine, iodine, nitro, cyano, methoxy or trifluoromethylsubstituents.

[0028] R⁴ with very particular preference represents phenyl in each caseoptionally substituted from one to four times by identical or differentmethyl, ethyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy,trifluoromethoxy, 2-methoxyethoxy or cyano substituents, two adjacentcarbon atoms optionally forming a five- or six-membered carbocycle whichmay optionally be interrupted by one or two oxygen atoms.

[0029] The definitions of radicals and/or elucidations given above orgiven in ranges of preference apply to the end products and to theprecursors and intermediates correspondingly. These definitions ofradicals may be combined as desired with one another, hence includingcombinations between the respective ranges of preference.

[0030] Preference in accordance with the invention is given to thecompounds of the formula (I) in which there is a combination of thedefinitions set out above as being preferred (preferably).

[0031] Particular preference in accordance with the invention is givento the compounds of the formula (I) in which there is a combination ofthe definitions set out above as being particularly preferred (withparticular preference).

[0032] Very particular preference in accordance with the invention isgiven to the compounds of the formula (I) in which there is acombination of the definitions set out above as being very particularlypreferred (with very particular preference).

[0033] In the definitions of radicals set out above and belowhydrocarbon radicals, such as alkyl, both alone and in conjunction withheteroatoms, such as alkoxy, are where possible in each casestraight-chain or branched.

[0034] Using, for example,1-amino-4,5-dimethyl-2-(3,5-dimethylphenyl)imidazole and 4-ethylbenzoylchloride as starting materials, the course of reaction in the process ofthe invention may be depicted by the following formula scheme:

[0035] A general definition of the compounds to be used as startingmaterials for carrying out the process of the invention is given by theformulae (II) and (III).

[0036] The compounds of the formula (II) are novel with the exception of1-amino-2-phenylimidazole, 1-amino-2-(4-chlorophenyl)imidazole,1-amino-2-(4-methoxy-phenyl)imidazole and1-amino-2-(3,4-dimethoxyphenyl)imidazole.

[0037] They may be obtained by subjecting compounds of the formula (IV)

[0038] in which

[0039] R¹, R² and R³ are as defined above and R⁶ denotes alkyl oroptionally substituted phenyl to hydrolytic cleavage with an acid, forexample, optionally in the presence of a diluent.

[0040] The compounds of the formula (IV) are likewise novel.

[0041] They may be obtained by reacting compounds of the formula (V)

[0042] in which R¹, R², R³ and R⁶ are as defined above

[0043] with a water-removing agent such as POCl₃, PCl₅ or SOCl₂, forexample, optionally in the presence of a diluent.

[0044] The compounds of the formula (V) are known in principle and maybe prepared in accordance with a process known from the literature(Liebigs Ann. Chem. 1978, 1916).

[0045] Some of the compounds of the formula (III) are novel.

[0046] The following compounds of the formula (III) are novel:

[0047] The compounds of the formula (III) may be prepared in accordancewith the Preparation Examples (III-1, III-2 and III-3).

[0048] The process of the invention is preferably carried out usingdiluents. Suitable diluents include virtually all inert organicsolvents. These include preferably aliphatic and aromatic, optionallyhalogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutylether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofuran and dioxane, ketones such as acetone, methyl ethylketone, methyl isopropyl ketone or methyl isobutyl ketone, esters suchas methyl or ethyl acetate, nitrites such as acetonitrile orpropionitrile, for example, amides such as dimethylformamide,dimethylacetamide and N-methylpyrrolidone, for example, and alsodimethyl sulfoxide, tetramethylene sulfone or hexamethylphosphoramide.

[0049] As acid acceptors in the process of the invention it is possibleto use all acid binders which can commonly be used for such reactions.Those suitable include preferably alkali metal and alkaline earth metalhydrides, such as lithium, sodium, potassium or calcium hydride, alkalimetal or alkaline earth metal hydroxides, such as lithium, sodium,potassium or calcium hydroxide, alkali metal or alkaline earth metalcarbonates or bicarbonates, such as sodium or potassium carbonates orbicarbonate or calcium carbonate, alkali metal acetates, such as sodiumor potassium acetate, alkali metal alkoxides, such as sodium orpotassium tert-butoxide, and also basic nitrogen compounds, such astrimethylamine, triethylamine, tripropylamine, tributylamine,diisobutylamine, dicyclohexylamine, ethyldiisopropylamine,ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethylaniline,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine,1,5-diazabicyclo[4.3.0]non-5-ene (DBN),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or1,4-diazabicyclo[2.2.2]octane (DABCO).

[0050] As carboxylic-acid-activating reagent (coupling reagent) use ismade in the process of the invention of all those suitable for preparingan amide linkage (cf. e.g.: Houben-Weyl, Methoden der organischenChemie, Volume 15/2; Bodanszky et al., Peptide Synthesis 2nd ed. (Wiley& Sons, New York 1976) or Gross, Meienhofer, The Peptides: AnalysisSynthesis, Biology (Academic Press, New York 1979). It is preferred toemploy the following methods: active ester method with pentachlorophenol(Pcp) and pentafluorophenol (Pfp), N-hydroxysuccinimide,N-hydroxy-5-norbornene-2,3-dicarboxamide (HONB), 1-hydroxybenzotriazole(HOBt) or 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine as alcoholcomponent, coupling with carbodiimides such as dicyclohexylcarbodiimide(DCC) by the DCC additive process, or with n-propanephosphonic anhydride(PPA) and mixed-anhydride method using pivaloyl chloride, ethyl (EEDQ)and isobutyl (IIDQ) chloroformate or coupling with phosphonium reagents,such as benzotriazol-1-yloxytris(dimethylaminophosphonium)hexafluorophosphate (BOP), bis(2-oxo-3-oxazolidinyl)phosphonium chloride(BOP-Cl), or with phosphonic ester reagents, such as diethylcyanophosphonate (DEPC) and diphenylphosphoryl azide (DPPA) or uroniumreagents, such as 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumtetrafluoroborate (TBTU).

[0051] As basic reaction auxiliaries for carrying out the process of theinvention it is possible to use all suitable acid binders such asamines, especially tertiary amines, and also alkali metal compounds andalkaline earth metal compounds.

[0052] Examples thereof that may be mentioned include the hydroxides,oxides and carbonates of lithium, sodium, potassium, magnesium, calciumand barium, and also other basic compounds such as amidine bases orguanidine bases such as 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene(MTBD), diazabicyclo[4.3.0]nonene (DBN), diazabicyclo-[2.2.2]octane(DABCO), 1,8-diazabicyclo[5.4.0]undecene (DBU),cyclohexyltetra-butylguanidine (CyTBG), cyclohexyltetramethylguanidine(CyTMG), N,N,N,N-tetramethyl-1,8-naphthalenediamine,pentamethylpiperidine, tertiary amines such as triethylamine,trimethylamine, tribenzylamine, triisopropylamine, tributylamine,tribenzylamine, tricyclohexylamine, triamylamine, trihexylamine,N,N-dimethylaniline, N,N-dimethyltoluidine,N,N-dimethyl-p-aminopyridine, N-methylpyrrolidine, N-methylpiperidine,N-methylimidazole, N-methylpyrrole, N-methylmorpholine,N-methylhexamethyleneimine, pyridine, 4-pyrrolidinopyridine,4-dimethylaminopyridine, quinoline, α-picoline, isoquinoline,pyrimidine, acridine, N,N,N′,N′-tetramethylenediamine,N,N,N′,N′-tetraethylenediamine, quinoxaline, N-propyldiisopropylamine,N-ethyldiisopropylamine, N,N′-dimethylcyclohexylamine, 2,6-lutidine,2,4-lutidine or triethylenediamine.

[0053] The reaction temperatures in the process of the invention may bevaried within a relatively large range. It is normal to operate attemperatures between −20° C. and 80° C., preferably at temperaturesbetween 0° C. and 50° C.

[0054] The process of the invention is generally carried out underatmospheric pressure. It is, however, also possible to operate underincreased or reduced pressure.

[0055] For carrying out the process of the invention the particularrequisite starting materials are used generally in approximatelyequimolar amounts. It is, however, also possible to use one of the twocomponents used in each case in a relatively large excess. It may alsobe advantageous to operate with 2 or more equivalents of the compound ofthe formula (III). In this case the product is predominantly abisbenzoylated derivative, which in a second step is hydrolyticallycleaved to the monobenzoylated derivative. Workup in the processes ofthe invention takes place in each case in accordance with customarymethods (cf. Preparation Examples).

[0056] It has also been found that the novel compounds of the formula(I) are obtained if compounds of the formula (VI)

[0057] in which

[0058] R¹ and R² are as defined above

[0059] are reacted with compounds of the formula (VII)

R³CHO  (VII)

[0060] in which

[0061] R³ is as defined above and

[0062] compounds of the formula (VII)

R⁴CO NH NH₂  (VIII)

[0063] in which

[0064] R⁴ is as defined above

[0065] in the presence of a diluent at temperatures between 20° C. and160° C. and the resulting N-oxide derivative is reacted with zinc inglacial acetic acid at temperatures between 20° C. and 100° C. (Z. Chem.1971, 11, 10) or titanium tetrachloride and sodium iodide in thepresence of a diluent at temperatures between 0° C. and 60° C. (Chem.Ber. 1990, 123, 647) or trialkyl phosphite in the presence of a diluentat temperatures between 0° C. and 80° C. (JCS, 1962, 1917) or phosphorustrichloride in the presence of a diluent at temperatures between 10° C.and 100° C. (Tet. 1999, 55, 1441) or DDQ in the presence of a diluent attemperatures between 10° C. and 100° C. (Tet. 1999, 55, 1441) orTCNQ/TCNQF4 in the presence of a diluent at temperatures between 0° C.and 80° C. (J. Chem. Res. (S) 1999, 620).

[0066] The compounds of the formulae (VI), (VII) and (VIII) are known inprinciple and in many cases are indeed available commercially. Compoundsof the formula (VI) may be obtained, for example, in accordance withOrg. Syn. Coll. Vol. II, 204; compounds of the formula (VIII), forexample, in accordance with Pharmazie 1996, 51, 83.

[0067] The active compounds are suitable for controlling animal pests,in particular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may preferably beemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The above-mentioned pests include:

[0068] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0069] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0070] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spp.

[0071] From the order of the Symphyla, for example, Scutigerellaimmaculate.

[0072] From the order of the Thysanura, for example, Lepisma saccharina.

[0073] From the order of the Collembola, for example, Onychiurusarmatus.

[0074] From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

[0075] From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae and Blattella gemmanica.

[0076] From the order of the Dermaptera, for example, Forficulaauricularia.

[0077] From the order of the Isoptera ,for example, Reticulitermes spp.

[0078] From the order of the Phthiraptera, for example, Pediculushumanus corporis, Haematopinus spp., Linognathus spp., Trichoidectesspp. and Damalinia spp.

[0079] From the order of the Thysanoptera ,for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

[0080] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0081] From the order of the Homoptera ,for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0082] From the order of the Lepidoptera ,for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp. and Oulema oryzae.

[0083] From the order of the Coleoptera ,for example, Anobium punctatum,Rhizopertha dorninica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

[0084] From the order of the Hymenoptera ,for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0085] From the order of the Diptera ,for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

[0086] From the order of the Siphonaptera ,for example, Xenopsyllacheopis and Ceratophyllus spp.

[0087] From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp. and Brevipalpus spp.

[0088] The phytoparasitic nematodes include, for example, Pratylenchusspp., Radopholus similis, Ditylenchus dipsaci, Tylenchulussemipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.and Bursaphelenchus spp.

[0089] If appropriate, the compounds according to the invention can, atcertain concentrations or application rates, also be used as herbicidesor microbicides, for example as fungicides, antimycotics andbactericides. If appropriate, they can also be employed as intermediatesor precursors for the synthesis of other active compounds.

[0090] All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and including the plant cultivars protectable or not protectableby plant breeders' rights. Plant parts are to be understood as meaningall parts and organs of plants above and below the ground, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds,roots, tubers and rhizomes. The plant parts also include harvestedmaterial, and vegetative and generative propagation material, forexample cuttings, tubers, rhizomes, offshoots and seeds.

[0091] The treatment according to the invention of the plants and plantparts with the active compounds is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

[0092] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound and microencapsulations in polymericsubstances.

[0093] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, optionally with the use of surfactants,that is to say emulsifiers and/or dispersants and/or foam-formers.

[0094] If the extender used is water, it is also possible to employ forexample organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, and also water.

[0095] Suitable solid carriers are:

[0096] for example ammonium salts and ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates; suitable solid carriers forgranules are: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;suitable emulsifiers and/or foam-formers are: for example nonionic andanionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates and alsoprotein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

[0097] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

[0098] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0099] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0100] The active compounds according to the invention can be used assuch or in their formulations, including mixtures with known fungicides,bactericides, acaricides, nematicides or insecticides, so as, forexample, to broaden the spectrum of action or prevent resistancesdeveloping. In many cases here, synergistic effects are obtained, i.e.the activity of the mixture is greater than the activity of theindividual components.

[0101] Suitable co-components are, for example, the following compounds:

[0102] Fungicides:

[0103] aldimorph, ampropylfos, ampropylfos-potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0104] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0105] calcium polysulphide, carpropamid, capsimycin, captafol, captan,carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone,chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate,clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0106] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0107] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0108] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenhexamid, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentinacetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover,fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide,flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium,fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

[0109] guazatine,

[0110] hexachlorobenzene, hexaconazole, hymexazole,

[0111] imazalil, irnibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, iprovalicarb, irumamycin, isoprothiolane, isovaledione,

[0112] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0113] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0114] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0115] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,oxyfenthiin,

[0116] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

[0117] quinconazole, quintozene (PCNB), quinoxyfen,

[0118] sulphur and sulphur preparations, spiroxamine,

[0119] tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, toiclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichiamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

[0120] uniconazole,

[0121] validamycin A, vinclozolin, viniconazole,

[0122] zarilamide, zineb, ziram and also Dagger G,

[0123] OK-8705,

[0124] OK-8801,

[0125]α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0126]α-(2,4-dichlorophenyl)-α-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

[0127]α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

[0128]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0129](5RS)6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0130] (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0131]1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

[0132] 1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

[0133] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

[0134] 1-[(diiodomethyl)-sulphonyl]4-methyl-benzene,

[0135]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0136]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0137]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0138] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0139]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,

[0140] 2,6-dichloro-5-(methylthio)₄-pyrimidinyl-thiocyanate,

[0141] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0142] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0143] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0144]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0145]2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0146] 2-aminobutane,

[0147] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0148]2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0149] 2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0150] 2-phenylphenol (OPP),

[0151] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

[0152]3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

[0153] 3-(1,1-dimethylpropyl)-1-oxo-1H-indene-2-carbonitrile,

[0154] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0155]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0156] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0157] 8-hydroxyquinoline sulphate,

[0158] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0159]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

[0160] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0161]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl]-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

[0162] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0163] potassium bicarbonate,

[0164] methanetetrathiol-sodium salt,

[0165] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0166] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0167] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0168]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0169]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0170] N-(2-chloro-4-nitrophenyl)₄-methyl-3-nitro-benzenesulphonamide,

[0171] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0172] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0173]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0174] N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

[0175] N-[2,2,2-trichloro-1-[(chloroacetyl)-aniino]-ethyl]-benzamide,

[0176]N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methaneimidamide,

[0177] N-formyl-N-hydroxy-DL-alanine-sodium salt,

[0178] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0179] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0180] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0181] spiro[2H]-1-benzopyran-2,1′ (3′H)-isobenzofuran]-3′-one;

[0182] 4-[3,4-dimethoxyphenyl-3-(4-fluorophenyl)-acryloyl]-morpholine.

[0183] Bactericides:

[0184] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0185] Insecticides/acaricides/nematicides:

[0186] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0187]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,butocarboxim, butylpyridaben,

[0188] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidin, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

[0189] deltamethrin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0190] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0191] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,fubfenprox, furathiocarb,

[0192] granulosis viruses,

[0193] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0194] imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,ivernectin,

[0195] nuclear polyhedrosis viruses,

[0196] lambda-cyhalothrin, lufenuron,

[0197] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, monocrotophos,

[0198] naled, nitenpyram, nithiazine, novaluron,

[0199] omethoate, oxamyl, oxydemethon M,

[0200]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

[0201] quinalphos,

[0202] ribavirin,

[0203] salithion, sebufos, silafluofen, spinosad, spirodiclofen,sulfotep, suiprofos,

[0204] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb,

[0205] vamidothion, vaniliprole, Verticillium lecanii,

[0206] YI 5302,

[0207] zeta-cypermethrin, zolaprofos,

[0208](1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

[0209](3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

[0210]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0211]2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]4,5-dihydro-oxazole,

[0212] 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

[0213]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0214]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0215] 3-methylphenyl propylcarbamate,

[0216] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[0217]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[0218]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

[0219]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[0220]Bacillus thuringiensis strain EG-2348,

[0221] 2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[0222]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en4-ylbutanoate,

[0223][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[0224] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

[0225] ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)₄-pyridazinyl]oxy]ethyl]-carbamate,

[0226] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

[0227]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[0228] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[0229] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

[0230] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[0231] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0232] N-cyanomethyl-4-trifluoromethyl-nicotinamide,

[0233]3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene.

[0234] It is also possible to admix other known active compounds, suchas herbicides, fertilizers and growth regulators.

[0235] When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, ina mixture with synergistic agents.

[0236] Synergistic agents are compounds which increase the action of theactive compounds, without it being necessary for the synergistic agentadded to be active itself.

[0237] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0238] The compounds are employed in a customary manner appropriate forthe use forms.

[0239] When used against hygiene pests and pests of stored products, theactive compound is distinguished by an excellent residual action on woodand clay as well as a good stability to alkali on limed substrates.

[0240] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding methods, such as crossing or protoplastfusion, and parts thereof, are treated. In a further preferredembodiment, transgenic plants and plant cultivars obtained by geneticengineering, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove.

[0241] Particularly preferably, plants of the plant cultivars which arein each case commercially available or in use are treated according tothe invention. Plant cultivars are to be understood as meaning plantshaving new properties (“traits”) which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.These can be varieties, bio- and genotypes.

[0242] Depending on the plant species or plant cultivars, their locationand growth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichextend beyond the effects which were actually to be expected.

[0243] The preferred transgenic plants or plant cultivars (i.e. thoseobtained by genetic engineering) which are to be treated according tothe invention include all plants which, in the genetic modification,received genetic material which imparted particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapevines), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed in the plants by the genetic material from Bacillus thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits that are alsoparticularly emphasized are the increased defence of plants againstfungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combinations with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these or still to bedeveloped genetic traits, which plants will be developed and/or marketedin the future.

[0244] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants.

[0245] Particular emphasis is given to the treatment of plants with thecompounds or the mixtures specifically mentioned in the present text.

[0246] The active compounds according to the invention act not onlyagainst plant, hygiene and stored product pests, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, leaf mites, flies (bitingand licking), parasitic fly larvae, lice, hair lice, feather lice andfleas. These parasites include:

[0247] From the order of the Anoplurida ,for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0248] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

[0249] From the order of the Diptera andthe suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0250] From the order of the Siphonapterida ,for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0251] From the order of the Heteropterida ,for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0252] From the order of the Blattarida ,for example, Blatta orientalis,Periplaneta americana, Blattella germanica and Supella spp.

[0253] From the subclass of the Acaria (Acarida)and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0254] From the order of the Actinedida (Prostigmata)and Acaridida(Astigmata),for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0255] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reduction inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

[0256] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injections(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

[0257] When used for cattle, poultry, pets and the like, the activecompounds of the formula (I) can be used as formulations (for examplepowders, emulsions, free-flowing compositions), which comprise theactive compounds in an amount of 1 to 80% by weight, directly or after100 to 10 000-fold dilution, or they can be used as a chemical bath.

[0258] It has furthermore been found that the compounds according to theinvention have a strong insecticidal action against insects whichdestroy industrial materials.

[0259] The following insects may be mentioned as examples and aspreferences—but without a limitation:

[0260] Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis,Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis,Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus,Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. and Dinoderus minutus.

[0261] Hymenopterons, such as

[0262]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus andUrocerus augur.

[0263] Termites, such as

[0264]Kalotermes flavicollis, Cryptotermes brevis, Heteroternesindicola, Reticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis and Coptotermes formosanus.

[0265] Bristletails, such as Lepisma saccharina.

[0266] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cards, leather, wood andprocessed wood products and coating compositions.

[0267] Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

[0268] Wood and processed wood products which can be protected by theagent according to the invention or mixtures comprising it are to beunderstood as meaning, for example:

[0269] building timber, wooden beams, railway sleepers, bridgecomponents, boat jetties, wooden vehicles, boxes, pallets, containers,telegraph poles, wood panelling, wooden window frames and doors,plywood, chipboard, joinery or wooden products which are used quitegenerally in house-building or in building joinery.

[0270] The active compounds can be used as such, in the form ofconcentrates or in generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0271] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersing agent and/or binder or fixing agent,a water repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

[0272] The insecticidal compositions or concentrates used for theprotection of wood and wood-derived timber products comprise the activecompound according to the invention in a concentration of 0.0001 to 95%by weight, in particular 0.001 to 60% by weight.

[0273] The amount of the compositions or concentrates employed dependson the nature and occurrence of the insects and on the medium. Theoptimum amount employed can be determined for the use in each case byseries of tests. In general, however, it is sufficient to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

[0274] Solvents and/or diluents which are used are an organic chemicalsolvent or solvent mixture and/or an oily or oil-like organic chemicalsolvent or solvent mixture of low volatility and/or a polar organicchemical solvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

[0275] Organic chemical solvents which are preferably used are oily oroil-like solvents having an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C. Substances which are used as suchoily or oil-like water-insoluble solvents of low volatility areappropriate mineral oils or aromatic fractions thereof, or solventmixtures containing mineral oils, preferably white spirit, petroleumand/or alkylbenzene.

[0276] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum and aromatics having aboiling range from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

[0277] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 0.180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

[0278] The organic oily or oil-like solvents of low volatility whichhave an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., can be replaced in part by organic chemicalsolvents of high or medium volatility, provided that the solvent mixturelikewise has an evaporation number above 35 and a flashpoint above 30°C., preferably above 45° C., and that the insecticide/fungicide mixtureis soluble or emulsifiable in this solvent mixture.

[0279] According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

[0280] Organic chemical binders which are used in the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are known per se, are water-dilutable and/or are soluble ordispersible or emulsifiable in the organic chemical solvents employed,in particular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-coumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

[0281] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. Dyestuffs, pigments, water-repelling agents, odour correctantsand inhibitors or anticorrosive agents and the like which are known perse can additionally be employed.

[0282] It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkydresins having an oil content of more than 45% by weight, preferably 50to 68% by weight, are preferably used according to the invention.

[0283] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[0284] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[0285] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether or ketones, such asbenzophenone or ethylenebenzophenone.

[0286] Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

[0287] Particularly effective preservation of wood is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[0288] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[0289] Possible additional mixing partners are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[0290] Very particularly preferred mixing partners which may bementioned are insecticides, such as chlorpyriphos, phoxim, silafluofin,alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin,imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin,thiacloprid, methoxyfenozide and triflumuron, and also fungicides, suchas epoxyconazole, hexaconazole, azaconazole, propiconazole,tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid,tolylfluanid, 3-iodo-2-propinyl butylcarbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

[0291] The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with salt wateror brackish water, in particular hulls, screens, nets, buildings,moorings and signalling systems, against fouling.

[0292] Fouling by sessile Oligochaeta, such as Serpulidae, and by shellsand species from the Ledamoipha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

[0293] Apart from fouling by algae, for example Ectocarpus sp. andCeramium sp., fouling by sessile Entomostraka groups, which come underthe generic term Cirripedia (cirriped crustaceans), is of particularimportance.

[0294] Surprisingly, it has now been found that the compounds accordingto the invention, alone or in combination with other active compounds,have an outstanding antifouling action.

[0295] Using the compounds according to the invention, alone or incombination with other active compounds, allows the use of heavy metalssuch as, for example, in bis(trialkyltin) sulphides, tri-n-butyltinlaurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)-tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthio-carbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

[0296] If appropriate, the ready-to-use antifouling paints canadditionally comprise other active compounds, preferably algicides,fungicides, herbicides, molluscicides, or other antifouling activecompounds.

[0297] Preferably suitable components in combinations with theantifouling compositions according to the invention are:

[0298] algicides such as

[0299] 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

[0300] fungicides such as

[0301] benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

[0302] molluscicides such as

[0303] fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarband trimethacarb; or conventional antifouling active compounds such as4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmalei mide.

[0304] The antifouling compositions used comprise the active compoundaccording to the invention of the compounds according to the inventionin a concentration of 0.001 to 50% by weight, in particular 0.01 to 20%by weight.

[0305] Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

[0306] Besides the algicidal, fungicidal, molluscicidal active compoundsand insecticidal active compounds according to the invention,antifouling paints comprise, in particular, binders.

[0307] Examples of recognized binders are polyvinyl chloride in asolvent system, chlorinated rubber in a solvent system, acrylic resinsin a solvent system, in particular in an aqueous system, vinylchloride/vinyl acetate copolymer systems in the form of aqueousdispersions or in the form of organic solvent systems,butadiene/styrene/acrylonitrile rubbers, drying oils such as linseedoil, resin esters or modified hardened resins in combination with tar orbitumens, asphalt and epoxy compounds, small amounts of chlorine rubber,chlorinated polypropylene and vinyl resins.

[0308] If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

[0309] The active compounds are also suitable for controlling animalpests, in particular insects, arachnids and mites, which are found inenclosed spaces such as, for example, dwellings, factory halls, offices,vehicle cabins and the like. They can be employed alone or incombination with other active compounds and auxiliaries in domesticinsecticide products for controlling these pests. They are activeagainst sensitive and resistant species and against all developmentstages. These pests include:

[0310] From the order of the Scorpionidea ,for example, Buthusoccitanus.

[0311] From the order of the Acarina ,for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus andDermatophagoides forinae.

[0312] From the order of the Araneae ,for example, Aviculariidae andAraneidae.

[0313] From the order of the Opiliones ,for example, Pseudoscorpioneschelifer, Pseudoscorpiones cheiridium and Opiliones phalangium.

[0314] From the order of the Isopoda, for example, Oniscus asellus andPorcellio scaber.

[0315] From the order of the Diplopoda ,for example, Blaniulusguttulatus and Polydesmus spp.

[0316] From the order of the Chilopoda, for example, Geophilus spp.

[0317] From the order of the Zygentoma ,for example, Ctenolepisma spp.,Lepisma saccharina and Lepismodes inquilinus.

[0318] From the order of the Blattaria ,for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa and Supella longipalpa.

[0319] From the order of the Saltatoria, for example, Acheta domesticus.

[0320] From the order of the Dermaptera ,for example, Forficulaauricularia.

[0321] From the order of the Isoptera ,for example, Kalotermes spp. andReticulitermes spp.

[0322] From the order of the Psocoptera, for example, Lepinatus spp. andLiposcelis spp.

[0323] From the order of the Coleptera, for example, Anthrenus spp.,Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinusspp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais and Stegobium paniceum.

[0324] From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxyscalcitrans and Tipula paludosa.

[0325] From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella and Tineola bisselliella.

[0326] From the order of the Siphonaptera, for example, Ctenocephalidescanis, Ctenocephalides felis, Pulex irritans, Tunga penetrans andXenopsylla cheopis.

[0327] From the order of the Hymenoptera, for example, Camponotusherculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,Monomorium pharaonis, Paravespula spp. and Tetramorium caespitum.

[0328] From the order of the Anoplura, for example, Pediculus humanuscapitis, Pediculus humanus corporis and Phthirus pubis.

[0329] From the order of the Heteroptera, for example, Cimex hemipterus,Cimex lectularius, Rhodinus prolixus and Triatoma infestans.

[0330] In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

[0331] They are used as aerosols, unpressurized spray products, forexample pump and atomizer sprays, automatic misting systems, foggers,foams, gels, evaporator products with evaporator tablets made ofcellulose or polymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, unpowered or passive evaporation systems,moth papers, moth bags and moth gels, as granules or dusts, in baits forspreading or in bait stations.

PREPARATION EXAMPLES Example I-1

[0332]

[0333] A solution of p-ethylbenzoyl chloride (1.685 g, 10 mM) in 10 mlof absolute tetrahydrofuran (THF) is added under argon at 0° C. to thecompound from Preparation Example II-1 (1.075 g, 5 mM) and Hüinig's base(2.61 ml, 15 mM) in 10 ml of abs. THF and the mixture is stirred at 0°C. for 15 minutes and then at room temperature overnight. The reactionsolution is poured into pH 7 buffer and extracted 3× with ethyl acetate.The organic phase is dried and concentrated. The residue is dissolved in20 ml of methanol, 6 ml of concentrated sodium hydroxide solution areadded and the mixture is stirred at room temperature for 1 hour. It ispoured into water and the pH is adjusted to 7 using concentratedhydrochloric acid. It is extracted 3× with ethyl acetate. The organicphase is dried and concentrated.

[0334] Yield: 1.3 g (75% of theory), m.p. 234° C., logP (pH 2.3) 1.97.

Example I-2

[0335]

[0336] A mixture of benzaldehyde (3.18 g, 0.03 M), p-tolylic hydrazide(4.5 g, 0.03 M) and 2,3-butanedione monoxime (9.09 g, 0.09 M) in 90 mlof glacial acetic acid is heated under reflux overnight and thenconcentrated. The residue is taken up in dichloromethane/water, sodiumcarbonate solution is added and the organic phase is separated. Theorganic phase is washed with water, dried and concentrated. The crudeproduct (10.7 g) is extracted by stirring with ether and the solid (5.8g) is filtered off with suction. This solid (N-oxide) is washed withwater, filtered off with suction, extracted by stirring with ethylacetate/ethanol 3:1 and filtered off with suction again.

[0337] Yield (N-oxide): 3.7 g (38.4% of theory), m.p.:>250° C., logP (pH2.3) 1.51.

[0338] Sodium iodide (1.75 g, 0.0117 M) and, immediately thereafter, asolution of the above N-oxide (0.63 g, 0.00196 M) in 3 ml of absoluteacetonitrile are added to a solution of titanium tetrachloride (0.74 g,0.0039 M) in 10 ml of absolute acetonitrile.

[0339] The mixture is subsequently stirred at room temperature for 40minutes, water is added and the pH is adjusted to 7 using dilutepotassium hydroxide solution, the mixture is filtered and the filtrateis extracted with dichloromethane. The target product is recovered fromthe dichloromethane extract.

[0340] Yield: 0.23 g, m.p.: 280° C., logP (pH 7.5) 2.17.

[0341] In analogy to the examples and in accordance with the generalpreparation details, the compounds of the formula (I) indicated in TableI below are obtained: TABLE 1 (I)

Ex. logP No. R¹ R² R³ R⁴ (pH 2.3) 3 CH₃ CH₃

1.68 4 CH₃ CH₃

1.68 5 CH₃ CH₃

1.74 6 H CH₃

1.90 7 H CH₃

1.64 8 H H

1.51 9

2.42 (pH 7.5) 10 CH₃ CH₃

2.06 (pH 7.5) 11 CH₃ CH₃

2.05 (pH 7.5) 12 CH₃ CH₃

1.44 13 CH₃ CH₃

1.32 14 CH₃ CH₃

1.65 15 CH₃ CH₃

1.44 16 CH₃

1.96 17 CH₃ CH₃

1.53 18 CH₃ CH₃

1.23 19 CH₃ CH₃

1.77 20 H CH₃

1.67 21 H H

1.29 22 H CH₃

1.84 23 H CH₃

1.62 24 H H

1.60 25 H CH₃

1.54 26 H CH₃

1.48 27 H CH₃

1.75 28 H CH₃

1.67 29 H CH₃

1.52 30 H CH₃

1.60 31 H CH₃

1.50 32 H CH₃

1.48 33 H CH₃

1.61 34 H CH₃

1.61 35 H CH₃

1.47 36 H CH₃

1.47 37 H CH₃

1.41 38 H CH₃

1.52 39 H CH₃

1.34 40 H CH₃

1.54 41 H CH₃

1.46 42 H CH₃

1.42 43 H CH₃

1.27 44 H CH₃

1.24 45 H CH₃

1.49 46 H CH₃

1.47 47 H CH₃

1.39 48 H CH₃

1.35 49 H CH₃

1.47 50 H CH₃

1.45 51 H CH₃

1.51 52 H CH₃

1.56 53 H CH₃

1.40 54 H CH₃

1.48 55 H CH₃

1.62 56 H CH₃

1.49 57 H CH₃

1.56 58 H CH₃

1.68 59 H CH₃

1.61 60 H CH₃

1.66 61 H CH₃

1.76 62 H CH₃

1.88 63 H CH₃

1.59 64 H CH₃

1.80 65 CH₃ CH₃

1.53 66 CH₃ CH₃

1.68 67 CH₃ CH₃

1.85 68 H CH₃

2.21 (pH 7.5) 69 H CH₃

1.61 70 H CH₃

2.17 (pH 7.5) 71 H CH₃

2.35 (pH 7.5) 72 H CH₃

2.40 (pH 7.5) 73 H CH₃

2.44 (pH 7.5) 74 H CH₃

2.46 (pH 7.5) 75 CH₃ CH₃

2.24 (pH 7.5) 76 CH₃ CH₃

2.25 (pH 7.5) 77 CH₃

1.79 78 CH₃

1.73 79 CH₃

1.94 80 CH₃ CH₃

2.48 (pH 7.5) 81 CH₃

2.18 82 CH₃ CH₃

1.53 83 CH₃ CH₃

2.35 (pH 7.5) 84 CH₃

1.88 85 CH₃ CH₃

2.61 (pH 7.5) 86 CH₃ CH₃

2.25 (pH 7.5) 87 CH₃

1.93 88 CH₃ CH₃

2.38 (pH 7.5) 89 CH₃ CH₃

1.52 90 CH₃ CH₃

2.06 (pH 7.5) 91 CH₃

2.46 92 CH₃ CH₃

2.39 (pH 7.5) 93 CH₃ CH₃

1.41 94 CH₃

2.28 95 CH₃

1.97 96 CH₃ CH₃

1.72 97

1.87 98

Example II-1

[0342]

[0343] Concentrated H₂SO₄ (100 ml) is added to the compound fromPreparation Example IV-1 (10 g, 0.0271 M) and the mixture is stirred atRT for 3 h, poured very slowly onto a large quantity of ice, renderedalkaline with 10% NaOH and extracted 3× with ethyl acetate.

[0344] Yield: 4.73 g (81% of theory), logP (pH 2.3) 0.96.

Example III-1

[0345]

[0346] Benzyltrimethylammonium hydroxide (40% strength solution inmethanol, 10 g; 0.06M) is added slowly dropwise at −10° C. to a mixtureof 2,5-dimethylphenol (60 g; 0.491M) and acrylonitrile (156.9 g;2.957M). The mixture is slowly brought to room temperature, then boiledunder reflux for 3 days and concentrated. The residue is washed withdilute sodium chloride solution and extracted with chloroform.

[0347] This gives 105.93 g of the crude product B1 (purity 71% by GC/MS,remainder starting phenol).

[0348] The crude product B1 (50 g, 0.2026M) is introduced dropwise at180-185° C. into rapidly stirred polyphosphoric acid (84% strength, 1028 g) and the mixture is held at this temperature for 2.5 h. The hotreaction mixture is poured into ice-water and extracted with chloroform.

[0349] This gives 22.9 g of the crude product C1 (purity 89% by LC/MS).

[0350] The crude product C1 (22.9 g, 0.1157M), dissolved in 130 ml oftrifluoroacetic acid, is admixed dropwise at room temperature withtriethylsilane (66.86 g; 0.575M) and the mixture is stirred for 33 h,poured onto ice and extracted with chloroform. The crude product ispurified by chromatography (silica gel, cyclohexane).

[0351] This gives 11.13 g of the compound D1 (purity 85% by GC/MS).

[0352] The compound D1 (16.0 g, 0.084M), dissolved in 150 ml ofanhydrous chloroform, is admixed at 0° C. with a spatula tip ofaluminium chloride and then with bromine (4.32 ml; 0.0839M); thetemperature is held below 4° C. during the addition. The mixture issubsequently stirred at room temperature for 1 h, water is added, andthe mixture is extracted with chloroform.

[0353] Purification of the extract by column chromatography (silica gel,cyclohexane) gives 18.3 g of the compound El (purity 95% by GC/MS).

[0354] The compound El (18.0 g, 0.071M) is dissolved in 200 ml ofanhydrous THF, the solution is cooled to −70° C. under argon,n-butyllithium (15% strength in hexane, 46.22 ml; 0.075M) is addeddropwise, and the mixture is stirred at −70° C. for 1 h and then pouredonto dry ice. After 8 h, water is added, acidification is carried outwith dilute hydrochloric acid and the solid is filtered off withsuction.

[0355] This gives 11.44 g of the compound III-1 (purity 98% by LC/MS),m.p. 211.5° C.

Example III-2

[0356]

[0357] Morpholine (86 g; 0.987M) and formaldehyde (35% strength solutionin water, 86 g; IM) in 250 ml of isopropanol are boiled under reflux for10 minutes and cooled to 0° C. and a solution of 3-methylpyrocatechol(124 g; IM) in 400 ml of isopropanol is added dropwise over the courseof 15 minutes. The reaction mixture is boiled under reflux for 15minutes, cooled and concentrated in vacuo and the residue isrecrystallized from isopropanol.

[0358] This gives 156.5 g of the compound B2 (purity 99% by LC/MS).

[0359] The compound B2 (117.44 g; 0.526M) is dissolved in 2 1 ofethanol, 48 g of 10% palladium on charcoal are added and the mixture ishydrogenated at 80° C. overnight under 60 bar of hydrogen. Thehydrogenation mixture is freed from the catalyst by filtration overKieselguhr, the filtrate is concentrated in vacuo, the residue isdissolved in chloroform and the solution is washed in succession withdilute hydrochloric acid and saturated sodium chloride solution, driedand concentrated in vacuo.

[0360] This gives 34.02 g of the compound C2 (purity 85% by LC/MS).

[0361] A suspension of the compound C2 (36.061 g, 0.222M) and dried,powdered potassium carbonate (108.2 g; 0.783M) in 250 ml of abs. DMF isheated to 110° C. under argon and dibromoethane (147.1 g; 0.783M) isadded dropwise over 2 h. After the end of the addition, heating iscontinued at 110° C. for 30 minutes, the mixture is cooled and filteredwith suction, the filtrate is concentrated in vacuo and the residue isdissolved in chloroform and washed 2× with dilute sodium hydroxidesolution and 1× with saturated sodium chloride solution.

[0362] This gives 35.7 g of the compound D2 (purity 83% by LC/MS).

[0363] N-Bromosuccinimide (22.521 g; 0.1265M) is added at −30° C. to thecompound D2 (22.891 g; 0.116M) in solution in 450 ml of anhydrousacetonitrile, cooling is removed and the batch is stirred overnight,filtered and concentrated in vacuo. The crude product is purified twiceby column chromatography (silica gel, cyclohexane).

[0364] This gives 11.6 g of the compound E2 (purity 88% by GC/MS).

[0365] n-Butyllithium (15% strength in hexane, 29.58 ml; 0.048M) isadded dropwise at −70° C. to the compound E2 (11.6 g, 0.042M) in 100 mlof anhydrous THF and the mixture is stirred at −70° C. for 1 h, thenpoured onto dry ice and left to stand overnight. Dilute sodium hydroxidesolution is added to the residue, the mixture is washed 2× with ether,and acidified with concentrated hydrochloric acid, and the solid isfiltered off with suction and dried.

[0366] This gives 6.56 g of the compound III-2 (purity 86% by BPLC,contaminated with 12% of 5,7,8-trimethyl-1,4-benzodioxane-6-carboxylicacid), m.p. 202-3° C.

Example III-3

[0367]

[0368] Iodoethane (78 g; 0.5M) is added to a suspension of2,5-dimethylphenol (40 g; 0.327M) and dried, powdered potassiumcarbonate (45.8 g; 0.331M) in 70 ml of anhydrous acetone and the mixtureis heated and stirred under reflux overnight. After cooling, water isadded to the reaction mixture and extraction is carried out 2× withdichloromethane. The combined organic phases are washed 2× with 10%strength sodium hydroxide solution, 1× with saturated sodium chloridesolution, dried and concentrated in vacuo.

[0369] This gives 40.25 g of the compound B3 (purity 99% by HPLC).

[0370] A solution of the compound B3 (40.25 g; 0.268M) in 450 ml ofanhydrous chloroform is cooled to 0° C., and a spatula tip of aluminiumchloride followed dropwise by bromine (16.8 ml; 0.326M) are added. Themixture is stirred at 0° C. for 1 h, then stirred at room temperaturefor 1 h, water is added and the chloroform phase is separated off.Washing is carried out with sodium bicarbonate solution and sodiumchloride solution and the washed mixture is dried and concentrated invacuo. It is then purified by column chromatography (silica gel,cyclohexane).

[0371] This gives 29.22 g of the compound C3 (purity 99% by BPLC).

[0372] A solution of the compound C3 (28.2 g; 0.123M) in 250 ml ofanhydrous THF is cooled to −60° C. under argon, n-butyllithium (15%strength in hexane, 90 ml; 0.146M) is added dropwise, and the mixture isthen stirred at −60° C. for 1.5 h and subsequently poured onto dry ice.It is left to stand overnight, water is added to the residue, themixture is acidified with concentrated hydrochloric acid and the solidis filtered off with suction.

[0373] This gives 18.05 g of the compound III-3 (purity 98% by HPLC),m.p. 178° C.

Example IV-1

[0374]

[0375] The compound from Preparation Example V-1 (32.3 g, 0.08346 M) andPOCl₃ (15.5 ml, 0.16692 M) are stirred under reflux in 650 ml ofabsolute chloroform for 3 hours. A further 15.5 ml of POCl₃ are addedand the mixture is stirred under reflux overnight. With ice cooling, 450ml of water are carefully added to the reaction solution which isstirred for 2 hours before 3 1 of saturated NaHCO₃ solution are slowlyadded. The organic phase is separated off and the aqueous phase isextracted 2× with chloroform. The organic phases are dried andconcentrated. The product is purified by column chromatography on silicagel (cyclohexane/ethyl acetate 1:2+a little CHCl₃).

[0376] Yield: 27.18 g (88% of theory), logP (pH 2.3) 1.69.

[0377] In analogy to the examples and in accordance with the generalpreparation details, the compounds of the formula (IV) indicated inTable 2 below are obtained: TABLE 2 (IV)

logP Ex. No. R¹ R² R³ R⁶ (pH 2.3) 2 H CH₃

1.63 3 CH₃ CH₃

1.43 4 H CH₃

1.57 5 H CH₃

1.48 6 H CH₃

1.92 7 H CH₃

1.59 8 H CH₃

1.62 9 H CH₃

1.59 10 H CH₃

1.65 11 H CH₃

1.39 12 CH₃ CH₃

1.56 13 H CH₃

1.93 14 H CH₃

15 H CH₃

1.59 16 H CH₃

1.76 17 H CH₃

1.69 18 H CH₃

1.68 19 H CH₃

1.56 20 CH₃

1.81 (pH 7.5)

Example V-1

[0378]

[0379] 3,5-Dimethylbenzoyl chloride (42.1 g, 0.25 M) is added dropwiseover the course of 2 hours at 10-15° C. to a solution of DL-alanine(44.55 g, 0.5 M) in 450 ml of 10% strength aqueous sodium hydroxidesolution. The solution is neutralized with concentrated hydrochloricacid. The precipitate is filtered off with suction, washed with waterand dried azeotropically in toluene on a water separator.

[0380] Yield (compound A): 29.5 g (53% of theory).

[0381] 5 g of the compound A, DMAP (0.11 g, 0.9 mM), acetic anhydride(4.52 ml, 0.04746 M) and triethylamine (4.52 ml, 0.0327 M) are stirredat room temperature.

[0382] After 30 minutes 34 ml of glacial acetic acid are added to thereaction solution which is then left to stand for 30 minutes. Thesolvent is distilled off, the precipitate is taken up in water, themixture is rendered alkaline using 2N sodium hydroxide and extractedwith ether. The organic phase is washed with 1N hydrochloric acidsolution and dried. The product is purified by column chromatography onsilica gel (cyclohexane/ethyl acetate, 3/1).

[0383] Yield (compound B): 3.73 g (75% of theory), logP (pH 2.3) 1.93.17 g of the compound B from the above batch, p-toluenesulfonyl hydrazide(14.38 g, 0.0776 M) and a spatula tip of PTSS are boiled in 1.81 ofbenzene on a water separator for 4 h and stirred at 0° C. for 15minutes. The precipitate is filtered off with suction, washed with coldbenzene and dried.

[0384] Yield: 27.3 g (91% of theory).

[0385] The crude product is reacted without further purification.

[0386] The logP values indicated were determined in accordance with EECDirective 79/831 Annex V.A8 by means of HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18). Temperature: 43° C.

[0387] (a) Eluents for determination in the acidic range: 0.1% aqueousphosphoric acid, acetonitriie; linear gradient from 10% acetonitrile to90% acetonitrile.

[0388] (b) Eluents for determination in the neutral range: 0.01 molaraqueous phosphate buffer solution, acetonitrile; linear gradient from10% acetonitrile to 90% acetonitrile.

[0389] Calibration was carried out with unbranched alkan-2-ones (having3 to 16 carbon atoms) of known logP (logP values are determined on thebasis of the retention times by means of linear interpolation betweentwo successive alkanones).

[0390] The lambda max values were determined from the UV spectra from200 nm to 400 nm in the maxima of the chromatographic signals.

USE EXAMPLES Example A

[0391] Meloidogyne test Solvent: 30 parts by weight of dimethylformamideEmulsifier:  1 part by weight of alkylaryl polyglycol ether

[0392] To produce an appropriate preparation of active compound, 1 partby weight of active compound is mixed with the stated amounts of solventand emulsifier and then the concentrate is diluted with water to thedesired concentration.

[0393] Pots are filled with sand, active compound solution, Meloidogyneincognito egg/larvae suspension and lettuce seeds. The lettuce seedsgerminate and the plantlets develop. The galls develop on the roots.

[0394] After the desired period of time, the nematicidal activity isdetermined in % from the formation of galls. 100% means that no gallswere found; 0% denotes that the number of galls on the treated plantscorresponds to the untreated control.

[0395] In this test, at an exemplary active compound concentration of 20ppm, the compound from Preparation Example No. 1-52 exhibits a kill of100% after 14 days.

Example B

[0396] Phaedon larvae test Solvent: 30 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

[0397] To produce an appropriate preparation of active compound, 1 partby weight of active compound is mixed with the stated amounts of solventand emulsifier and then the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0398] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound at the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still wet.

[0399] After the desired period of time, the kill in % is determined.100% means that all the beetle larvae were killed, 0% means that nobeetle larvae were killed.

[0400] In this test, at an exemplary active compound concentration of 1000 ppm, the compound from Preparation Example No. I-82 exhibits a killof 100% after 7 days.

Example C

[0401] Spodoptera frugiperda test Solvent: 30 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

[0402] To produce an appropriate preparation of active compound, 1 partby weight of active compound is mixed with the stated amounts of solventand emulsifier and then the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0403] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound at the desired concentration andare populated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still wet.

[0404] After the desired period of time, the kill in % is determined.100% means that all the caterpillars were killed, 0% means that nocaterpillars were killed.

[0405] In this test, at an exemplary active compound concentration of 1000 ppm, the compounds from Preparation Examples Nos. I-48, I-54, I-60,I-61, I-63, I-65, I-66, I-69, I-82 exhibit a kill of 100% after 7 days.

Example D

[0406] Tetranychus test (OP resistant/dip treatment) Solvent: 30 partsby weight of dimethylformamide Emulsifier:  1 part by weight ofalkylaryl polyglycol ether

[0407] To produce an appropriate preparation of active compound, 1 partby weight of active compound is mixed with the stated amounts of solventand emulsifier and then the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0408] Bean plants (Phaseolus vulgaris) heavily infested by all stagesof the common spider mite (Tetranychus urticae) are dipped into apreparation of the active compound at the desired concentration.

[0409] After the desired period of time, the effect in % is determined.100% means that all the spider mites were killed, 0% means that nospider mites were killed.

[0410] In this test, at an exemplary active compound concentration of100 ppm, the compound from Preparation Example No. 1-4 exhibits a killof 100% after 7 days.

Example E

[0411] Aedes test Solvent: 1 000 parts by weight of methanol

[0412] To produce an appropriate preparation of active compound, 1 partby weight of active compound is mixed with the stated amount of solventand the concentrate is diluted with a 0.01% strength lecithin solutionto the desired concentrations.

[0413] Midge larvae (Aedes aegypti) are placed into the preparation ofactive compound at the desired concentration.

[0414] After the desired period of time, the effect on the larvae isdetermined. 100% means that all of the midges showed severe symptoms orhave been killed, 0% means that no midges were harmed.

[0415] In this test, at an exemplary active compound concentration of 17ppm, the compound from Preparation Example No. I-19 exhibits a kill of100% after 4 hours.

Example F

[0416] Blowfly larvae test/development inhibition activity Testorganisms: Lucilia cuprina larvae Solvent: Dimethyl sulphoxide

[0417] 20 mg of active compound are dissolved in 1 ml of dimethylsulphoxide; lower concentrations are prepared by dilution with distilledH₂O.

[0418] About 20 Lucilia cuprina larvae are placed in a test tubecontaining about 1 cm³ of horse meat and 0.5 ml of the test activecompound preparation. After 24 and 48 hours the efficacy of the activecompound preparation is determined. The test tubes are transferred tobeakers with sand-covered bases. After a further 2 days the test tubesare removed and the pupae are counted.

[0419] The effect of the active compound preparation is assessedaccording to the number of hatched flies after one and a half times thedevelopment period of an untreated control. 100% means that none of theflies has hatched, 0% means that all of the flies hatched normally.

[0420] In this test, at an exemplary active compound concentration of 2500 ppm, the compounds from Preparation Examples Nos. 1-77, 1-78 and1-79 show that no flies hatched.

What is claimed is: 1-13. (Canceled)
 14. A compound of formula (I)

in which R¹ and R² independently of one another represent hydrogen,alkyl, alkoxyalkyl, alkylthioalkyl; represent optionally substitutedcycloalkyl; or represent optionally substituted heterocyclyl; or R¹ andR² together with the carbon atoms to which they are attached representan optionally substituted mono- or bicyclic, carbocyclic, orheterocyclic group, and R³ and R⁴ independently of one another representoptionally substituted aryl or hetaryl.
 15. A compound of formula (I)according to claim 14 in which R¹ and R² independently of one anotherrepresent hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₃-alkyl, orC₁-C₃-alkylthio-C₁-C₃-alkyl; or represent optionallyC₁-C₃-alkyl-substituted C₃-C₇-cycloalkyl, which may optionally beinterrupted by one or two oxygen and/or sulphur atoms; or R¹ and R²together with the carbon atoms to which they are attached representoptionally C₁-C₃-alkyl-substituted C₃-C₄-alkanediyl in which two carbonatoms that are not directly adjacent optionally form a further cyclicstructure that is optionally interrupted by one oxygen and/or sulphuratom, R³ represents phenyl or hetaryl, each of which is optionallysubstituted once or twice by identical or different C₁-C₄-alkyl,C₁-C₄-alkoxy, halogen, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano, nitro,C₁-C₄-alkylsulfonyl, C₁-C₄-halo-alkylsulfonyl, thioamide, or tetrazolesubstituents, and R⁴ represents phenyl that is optionally substitutedfrom one to four times by identical or different C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, halogen, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, or cyano substituents and in which two adjacent carbonatoms optionally form a five- or six-membered carbocycle that isoptionally interrupted by one or two oxygen atoms; or representshetaryl.
 16. A compound of formula (I) according to claim 14 in which R¹and R² independently of one another represent hydrogen, C₁-C₅-alkyl,C₁-C₃-alkoxy-C₁-C₃-alkyl, or C₁-C₃-alkylthio-C₁-C₃-alkyl; or representC₃-C₆-cycloalkyl; or R¹ and R² together with the carbon atoms to whichthey are attached represent C₃-C₄-alkanediyl that is optionallysubstituted from one to three times by identical or differentC₁-C₃-alkyl substituents and in which two carbon atoms not directlyadjacent optionally form a further cyclic structure that is optionallyinterrupted by an oxygen or sulphur atom, R³ represents phenyl, pyridyl,thienyl, furyl, or pyrimidinyl, each of which is optionally substitutedonce or twice by identical or different methyl, fluorine, chlorine,bromine, iodine, cyano, nitro, methoxy, trifluoromethyl,trifluoromethoxy, sulfonylmethyl, sulfonyltrifluoromethyl, thioamide, ortetrazole substituents, and R⁴ represents phenyl that is optionallysubstituted from one to four times by identical or different methyl,ethyl, fluorine, chlorine, bromine, trifluoromethyl, methoxy,trifluoromethoxy, ethoxymethyl ether, or cyano substituents and in whichtwo adjacent carbon atoms optionally form a five- or six-memberedcarbocycle that is optionally interrupted by one or two oxygen atoms.17. A compound of formula (I) according to claim 14 in which R¹represents hydrogen or methyl, R² represents hydrogen, methyl, ethyl, n-or isopropyl, n-, iso- or s-butyl, cyclopentyl, or cyclohexyl; or R¹ andR² together with the carbon atoms to which they are attached representC₃-C₄-alkanediyl that is optionally substituted once or twice by methylor represent C₄-alkanediyl in which two carbon atoms not directlyadjacent optionally form a further cyclic structure that is optionallyinterrupted by an oxygen atom, R³ represents phenyl that is optionallysubstituted once or twice by identical or different methyl, fluorine,chlorine, bromine, iodine, nitro, cyano, methoxy, or trifluoromethylsubstituents, and R⁴ represents phenyl that is optionally substitutedfrom one to four times by identical or different methyl, ethyl,fluorine, chlorine, bromine, trifluoromethyl, methoxy, trifluoromethoxy,2-methoxyethoxy, or cyano substituents and in which two adjacent carbonatoms optionally form a five- or six-membered carbocycle that isoptionally interrupted by one or two oxygen atoms.
 18. A process forpreparing a compound of formula (I) according to claim 14 comprisingreacting a compound of formula (II)

in which R¹, R² and R³ are as defined for formula (I) of claim 14, witha compound of formula (III) R⁵—COR⁴  (III) in which R⁴ is as defined forformula (I), and R⁵ represents halogen or hydroxyl in the presence of adiluent and an acid acceptor and/or a carboxylic-acid-activating reagent(coupling reagent) and optionally in the presence of a basic reactionauxiliary.
 19. A compound of formula (II)

in which R¹ and R² independently of one another represent hydrogen,alkyl, alkoxyalkyl, alkylthioalkyl; represent optionally substitutedcycloalkyl; or represent optionally substituted heterocyclyl; or R¹ andR² together with the carbon atoms to which they are attached representan optionally substituted mono- or bicyclic, carbocyclic, orheterocyclic group, and R³ represents optionally substituted aryl orhetaryl, with the exception of 1-amino-2-phenylimidazole,1-amino-2-(4-chlorophenyl)-imidazole,1-amino-2-(4-methoxyphenyl)imidazole and1-amino-2-(3,4-dimethoxyphenyl)imidazole.
 20. A compound of formula (II)according to claim 19

in which R¹ and R² independently of one another represent hydrogen,C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₃-alkyl, or C₁-C₃-alkylthio-C₁-C₃-alkyl;or represent optionally C₁-C₃-alkyl-substituted C₃-C₇-cycloalkyl, whichmay optionally be interrupted by one or two oxygen and/or sulphur atoms;or R¹ and R² together with the carbon atoms to which they are attachedrepresent optionally C₁-C₃-alkyl-substituted C₃-C₄-alkanediyl in whichtwo carbon atoms that are not directly adjacent optionally form afurther cyclic structure that is optionally interrupted by one oxygenand/or sulphur atom, and R³ represents phenyl or hetaryl, each of whichis optionally substituted once or twice by identical or differentC₁-C₄-alkyl, C₁-C₄-alkoxy, halogen, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,cyano, nitro, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, thioamide,or tetrazole substituents, with the exception of1-amino-2-phenylimidazole, 1-amino-2-(4-chlorophenyl)-imidazole,1-amino-2-(4-methoxyphenyl)imidazole and1-amino-2-(3,4-dimethoxyphenyl)imidazole.
 21. A compound of formula (IV)

in which R¹ and R² independently of one another represent hydrogen,alkyl, alkoxyalkyl, alkylthioalkyl; represent optionally substitutedcycloalkyl; or represent optionally substituted heterocyclyl; or R¹ andR² together with the carbon atoms to which they are attached representan optionally substituted mono- or bicyclic, carbocyclic, orheterocyclic group, R³ represents optionally substituted aryl orhetaryl, and R⁶ represents alkyl or optionally substituted phenyl.
 22. Acompound of formula (IV) according to claim 21

in which R¹ and R² independently of one another represent hydrogen,C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₃-alkyl, or C₁-C₃-alkylthio-C₁-C₃-alkyl;or represent optionally C₁-C₃-alkyl-substituted C₃-C₇-cycloalkyl, whichmay optionally be interrupted by one or two oxygen and/or sulphur atoms;or R¹ and R² together with the carbon atoms to which they are attachedrepresent optionally C₁-C₃-alkyl-substituted C₃-C₄-alkanediyl in whichtwo carbon atoms that are not directly adjacent optionally form afurther cyclic structure that is optionally interrupted by one oxygenand/or sulphur atom, R³ represents phenyl or hetaryl, each of which isoptionally substituted once or twice by identical or differentC₁-C₄-alkyl, C₁-C₄-alkoxy, halogen, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,cyano, nitro, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylsulfonyl, thioamide,or tetrazole substituents, and R⁶ represents alkyl or optionallysubstituted phenyl.
 23. A compound of formula (III)

in which R⁴ represents


24. A pesticide comprising one or more compounds of formula (I)according to claim 14 and one or more extenders and/or surface-activesubstances.
 25. A method of controlling animal pests comprising causinga compound of formula (I) according to claim 14 to act on a pest and/orits habitat.
 26. A process for preparing pesticides comprising mixing acompound of formula (i) according to claim 14 with one or more extendersand/or surface-active substances.